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    City: Chestertown, MD
    Listing Status: Active
    Map
    108 Properties Available In Chestertown

    108 Properties Available In Chestertown

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    • Beds (Most)
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    MD >Chestertown >
    Market Insights
    24295 LANGFORD RD, Chestertown, MD 21620
    1/71
    Open Sat 2:30PM-4:30PM

    $445,000

    2 Beds3 Baths1,857 SqFt

    24295 LANGFORD RD, Chestertown, MD 21620

    MLS# MDKE2006320

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    240 MERGANSER DR, Chestertown, MD 21620
    1/51
    Open Sat 12PM-2PM
    3D

    $399,000

    3 Beds2 Baths1,120 SqFt

    240 MERGANSER DR, Chestertown, MD 21620

    MLS# MDQA2016900

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    204 DOUBLE CREEK RD, Chestertown, MD 21620
    1/46
    Open Sat 11AM-1PM

    $565,000

    3 Beds3 Baths2,927 SqFt

    204 DOUBLE CREEK RD, Chestertown, MD 21620

    MLS# MDQA2015996

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    7989 QUAKER NECK RD, Chestertown, MD 21620
    1/90
    Open 6/13 11AM-1PM
    3D

    $2,200,000

    5 Beds5 Baths4,305 SqFt

    7989 QUAKER NECK RD, Chestertown, MD 21620

    MLS# MDKE2005590

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    22470 FAIRGALE FARM LN, Chestertown, MD 21620
    1/49
    New

    $1,450,000

    4 Beds5 Baths4,257 SqFt

    22470 FAIRGALE FARM LN, Chestertown, MD 21620

    MLS# MDKE2006502

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
    522 HIGH ST, Chestertown, MD 21620
    1/15
    New

    $450,000

    2 Beds3 Baths1,518 SqFt

    522 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2006614

    Listed by Benson & Mangold, LLC

    Bright MLS (BMLS)
    956 WASHINGTON AVE, Chestertown, MD 21620
    1/29
    Active

    $285,000

    3 Beds1 Bath1,248 SqFt

    956 WASHINGTON AVE, Chestertown, MD 21620

    MLS# MDKE2006394

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    110 S QUEEN ST, Chestertown, MD 21620
    1/30
    Active

    $525,000

    3 Beds2 Baths1,785 SqFt

    110 S QUEEN ST, Chestertown, MD 21620

    MLS# MDKE2006520

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    102 FLYING CLOUD DR, Chestertown, MD 21620
    1/41
    Active

    $339,900

    3 Beds3 Baths1,896 SqFt

    102 FLYING CLOUD DR, Chestertown, MD 21620

    MLS# MDKE2006586

    Listed by Long & Foster Real Estate, Inc.

    Bright MLS (BMLS)
    107 FLYING CLOUD DR, Chestertown, MD 21620
    1/51
    Active

    $395,000

    5 Beds4 Baths2,534 SqFt

    107 FLYING CLOUD DR, Chestertown, MD 21620

    MLS# MDKE2006510

    Listed by CENTURY 21 New Millennium

    Bright MLS (BMLS)
    304 HADAWAY DR, Chestertown, MD 21620
    1/38
    Price Dropped by $7K
    3D

    $322,500

    4 Beds2 Baths1,325 SqFt

    304 HADAWAY DR, Chestertown, MD 21620

    MLS# MDKE2006482

    Listed by Redfin Corporation

    Bright MLS (BMLS)
    214 SILVER HEEL RD, Chestertown, MD 21620
    1/26
    Active

    $350,000

    4 Beds3 Baths1,972 SqFt

    214 SILVER HEEL RD, Chestertown, MD 21620

    MLS# MDKE2006498

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    407 HIGH ST, Chestertown, MD 21620
    1/57
    Price Dropped by $30K

    $798,000

    3 Beds5 Baths3,047 SqFt

    407 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2006496

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    103 TRAFFORD DR, Chestertown, MD 21620
    1/66
    Price Dropped by $30K

    $419,900

    3 Beds3 Baths1,944 SqFt

    103 TRAFFORD DR, Chestertown, MD 21620

    MLS# MDKE2006416

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    24581 WILLOW OAK LN, Chestertown, MD 21620
    1/29
    Active

    $229,990

    3 Beds2 Baths1,352 SqFt

    24581 WILLOW OAK LN, Chestertown, MD 21620

    MLS# MDKE2006342

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    205 RIVER RD, Chestertown, MD 21620
    1/72
    Price Dropped by $20K

    $899,500

    4 Beds3 Baths2,877 SqFt

    205 RIVER RD, Chestertown, MD 21620

    MLS# MDQA2016560

    Listed by Clark & Co Realty, LLC

    Bright MLS (BMLS)
    103 METCALF RD, Chestertown, MD 21620
    1/22
    Active

    $259,900

    3 Beds2 Baths1,280 SqFt

    103 METCALF RD, Chestertown, MD 21620

    MLS# MDKE2006446

    Listed by Real Broker, LLC - Chester

    Bright MLS (BMLS)
    8706 ELM RD, Chestertown, MD 21620
    1/7
    Active

    $320,000

    3 Beds2 Baths1,232 SqFt

    8706 ELM RD, Chestertown, MD 21620

    MLS# MDKE2006390

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    208 CENTRAL DR, Chestertown, MD 21620
    1/16
    Price Dropped by $16K

    $299,000

    3 Beds1 Bath1,120 SqFt

    208 CENTRAL DR, Chestertown, MD 21620

    MLS# MDQA2016836

    Listed by Redfin Corp

    Bright MLS (BMLS)
    21217 TEXAS AVE, Chestertown, MD 21620
    1/20
    Price Dropped by $20K

    $244,500

    2 Beds1 Bath912 SqFt

    21217 TEXAS AVE, Chestertown, MD 21620

    MLS# MDKE2006364

    Listed by RE/MAX Leading Edge

    Bright MLS (BMLS)
    226 S WATER ST, Chestertown, MD 21620
    1/31
    Active

    $898,000

    3 Beds4 Baths2,172 SqFt

    226 S WATER ST, Chestertown, MD 21620

    MLS# MDKE2006354

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
    103 SUTTON WAY, Chestertown, MD 21620
    1/53
    Active

    $550,000

    5 Beds4 Baths3,816 SqFt

    103 SUTTON WAY, Chestertown, MD 21620

    MLS# MDKE2006344

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    106 QUEEN ST S, Chestertown, MD 21620
    1/92
    Active

    $865,000

    3 Beds4 Baths2,472 SqFt

    106 QUEEN ST S, Chestertown, MD 21620

    MLS# MDKE2006152

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    104 FLYING CLOUD DR, Chestertown, MD 21620
    1/30
    Price Dropped by $5K

    $394,900

    5 Beds4 Baths2,535 SqFt

    104 FLYING CLOUD DR, Chestertown, MD 21620

    MLS# MDKE2006212

    Listed by Real Broker, LLC - Chester

    Bright MLS (BMLS)
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    Bayside Realty
    Dale Hunter Jr
    +1(443) 829-5828
    dalehunterjr@baysiderealtymd.com
    23458 Scotts Ln, St Michaels, MD, 21663, USA
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        Market Snapshot
    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

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    Bayside Realty
    Dale Hunter Jr
    +1(443) 829-5828
    dalehunterjr@baysiderealtymd.com
    23458 Scotts Ln, St Michaels, MD, 21663, USA
        Home
        Buy
        1. All Listings
        2. Featured Listings
        Sell
        1. Sell My Home
        2. Home Valuation
        3. Recent Sold
        Rent
        1. Rental Listings
        Featured Areas
        1. Easton Overview
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        5. Saint Michaels Overview
        6. Ridgely Overview
        7. Berlin Overview
        About
        1. My Team
        2. About Us
        3. Contact Us
        4. Reviews
        Market Snapshot
    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility